2-Benzo[1,3]dioxol-5-yl-6-isopropoxy-4-(5-methyl-thiophen-2-yl)-2H-chromene-3-carboxylic acid

ID: ALA293012

Chembl Id: CHEMBL293012

PubChem CID: 9868379

Max Phase: Preclinical

Molecular Formula: C25H22O6S

Molecular Weight: 450.51

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(C2=C(C(=O)O)C(c3ccc4c(c3)OCO4)Oc3ccc(OC(C)C)cc32)s1

Standard InChI:  InChI=1S/C25H22O6S/c1-13(2)30-16-6-8-18-17(11-16)22(21-9-4-14(3)32-21)23(25(26)27)24(31-18)15-5-7-19-20(10-15)29-12-28-19/h4-11,13,24H,12H2,1-3H3,(H,26,27)

Standard InChI Key:  FSKVJGRQYIHVTI-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA293012

   2-Benzo[1,3]dioxol-5-yl-6-isopropoxy-4-(5-methyl-thiophen-2-yl)-2H-chromene-3-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 450.51

Molecular Weight (Monoisotopic): 450.1137

AlogP: 5.59

#Rotatable Bonds: 5

Polar Surface Area: 74.22

Molecular Species: ACID

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 2.59

CX Basic pKa: ┄

CX LogP: 5.63

CX LogD: 2.12

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.55

Np Likeness Score: -0.25

References

1. Ishizuka N, Matsumura K, Sakai K, Fujimoto M, Mihara S, Yamamori T..  (2002)  Structure-activity relationships of a novel class of endothelin-A receptor antagonists and discovery of potent and selective receptor antagonist, 2-(benzo[1,3]dioxol-5-yl)-6-isopropyloxy-4-(4-methoxyphenyl)-2H-chromene-3-carboxylic acid (S-1255). 1. Study on structure-activity relationships and basic structure crucial for ET(A) antagonism.,  45  (10): [PMID:11985472] [10.1021/jm010382z]

2. Boss C, Bolli MH, Gatfield J..  (2016)  From bosentan (Tracleer®) to macitentan (Opsumit®): The medicinal chemistry perspective.,  26  (15): [PMID:27321813] [10.1016/j.bmcl.2016.06.014]

Source

Source(1):

• Scientific Literature